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Key West Watersports w/BobbyB

All Key West Tourist Watersports Private Charter Agent "There is magic in Key West...if you believe..."
Open today until 5:00 PM
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The 2022
Wreckers Race Series

Now so you can actually be in this exciting race on a fantastic wooden schooner just like sailors of yore, complete with grub and grog!
Reserve now! Seating is limited!


2022 and business is booming. Here are a couple tips.

Take shuttle services if offered where you will be staying. Parking in Key West is limited and expensive.
If you must drive allow 20 minutes to find parking. Everyday I see people miss their scheduled excursions due to parking. Companie...

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Happy Holidays...
Covid up date here @ KWWSBobbyB
I don't judge... My self. I am boosted, I wash my hands good, wear a mask when I feel it is appropriate, I social distance when I can. I keep my work area and public access pitch books clean and wiped down. Hand sanitizer is offered to all my clie...

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Christmas Season in Key West
A unique time on our Island
Book watersport here for Live Personalized Service
We will make sure you have all you need to know to have a Jolly time.
( Little tips like; Allow 20 minutes for parking if you are not using a shuttle.) And other important little details yo...

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Key West Schooner Sailing
The air is crisp, the winds are up, a sea of green and sky's of blue. The traditional wooden schooners are ready for you to sail away....
Text BobbyB
"Your Friend In Key West"

Key West Parasailing
The most relaxing Xtreme Sport!
Text us to reserve your seats.
Boats leave every hour on the hour.
"Your Friend In Key West"



2 weeks ago
Bobby B is the man for the best sailing hookup in town! Highly recommend sailing with Capt. Matt and crew for a really unforgettable sunset cruise!
- James M
3 months ago
I was in a bind because my original sunset cruise was cancelled less than 24 hours before it was suppose to happen. Key West Watersports with Bobby G. came through. Their customer service and follow through was excellent. We thoroughly enjoyed the sunset sailing cruise. The sailing crew was responsive; the snacks delicious and overall it was amazing. Thank you! I highly recommend them.
- Kathy L
a month ago
We booked a private cruise around the Island. The Captain was excellent and made it special. Gave us lots of information on sights and the boat was clean & comfortable. The boat left on the agreed schedule and the price was as agreed. Can’t think of any negatives or improvements to suggest. Highly recommend this booking service.
- Bob G

Live Personalized Attention To You

Personal live service for all your Key West Vacation Watersports under one umbrella ⛱️.

Contact Us


Call now
  • (305) 923-9533


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201 William St
Key West, FL 33040
United States

Business Hours

Mon:8:30 AM – 6:30 PM
Tue:9:00 AM – 5:00 PM
Wed:9:00 AM – 5:00 PM
Thu:7:30 AM – 7:30 PM
Fri:8:30 AM – 8:30 PM
Sat:8:00 AM – 8:00 PM
Sun:8:00 AM – 6:30 PM
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